Betulinic acid

Betulinic acid is a naturally occurring pentacyclic triterpenoid which has antiretroviral, antimalarial, and anti-inflammatory properties, as well as a more recently discovered potential as an anticancer agent, by inhibition of topoisomerase. It is found in the bark of several species of plants, principally the white birch (Betula pubescens) from which it gets its name, but also the ber tree (Ziziphus mauritiana), selfheal (Prunella vulgaris), the tropical carnivorous plants Triphyophyllum peltatum and Ancistrocladus heyneanus, Diospyros leucomelas, a member of the persimmon family, Tetracera boiviniana, the jambul (Syzygium formosanum), flowering quince (Pseudocydonia sinensis, former Chaenomeles sinensis KOEHNE), rosemary, and Pulsatilla chinensis.

Betulinic acid
Names
IUPAC name
3β-Hydroxylup-20(29)-en-28-oic acid
Systematic IUPAC name
(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-Hydroxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-1-yl)icosahydro-3aH-cyclopenta[a]chrysene-3a-carboxylic acid
Other names
Betulic acid
Mairin
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.006.773
EC Number
  • 207-448-8
PubChem CID
UNII
  • InChI=1S/C30H48O3/c1-18(2)19-10-15-30(25(32)33)17-16-28(6)20(24(19)30)8-9-22-27(5)13-12-23(31)26(3,4)21(27)11-14-29(22,28)7/h19-24,31H,1,8-17H2,2-7H3,(H,32,33)/t19-,20+,21-,22+,23-,24+,27-,28+,29+,30-/m0/s1 Y
    Key: QGJZLNKBHJESQX-FZFNOLFKSA-N Y
  • InChI=1/C30H48O3/c1-18(2)19-10-15-30(25(32)33)17-16-28(6)20(24(19)30)8-9-22-27(5)13-12-23(31)26(3,4)21(27)11-14-29(22,28)7/h19-24,31H,1,8-17H2,2-7H3,(H,32,33)/t19-,20+,21-,22+,23-,24+,27-,28+,29+,30-/m0/s1
    Key: QGJZLNKBHJESQX-FZFNOLFKBI
SMILES
  • O=C(O)[C@@]54[C@@H]([C@@H]3[C@@]([C@]1([C@@H]([C@]2(C)[C@@H](CC1)C(C)(C)[C@@H](O)CC2)CC3)C)(C)CC4)[C@H](C(=C)C)CC5
Properties
C30H48O3
Molar mass 456.711 g·mol−1
Melting point 316 to 318 °C (601 to 604 °F; 589 to 591 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references
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